Plant growth control



United States Patent 3,506,433 PLANT GROWTH CONTROL Walter W. Abramitis, Downers Grove, and Richard A. Reck, Hinsdale, Ill., assignors, by mesne assignments, to Armour Industrial Chemical Company, a corporation of Delaware No Drawing. Continuation-impart of application Ser. No. 206,196, June 29, 1962. This application Oct. 20, 1965, Ser. No. 499,032 The portion of the term of the patent subsequent to Dec. 14, 1982, has been disclaimed Int. Cl. A01n 5/00, 9/20 US. CI. 71-78 42 Claims ABSTRACT OF THE DISCLOSURE The control of undesirable secondary growth in plants with certain primary, secondary or tertiary amine salts.

This is a continuation-in-part of our copending application Ser. No. 206,196, filed June 29, 1962, now US. Patent No. 3,223,517.

This invention relates to plant growth control, and more particularly to the control of undesirable secondary growth in plants.

In various plants, such as, for example, tobacco, tomato, cotton, soybean plants, etc., undesirable secondary growth, which is generally referred to as suckers, creates a serious problem because the suckers develop rapidly to shade desired portions of the plant and tend to ruin the quality of such desired portions. In the tobacco plant, secondary buds form at the points where the leaf stems join the plant, and later after the flower is removed grow rapidly to form sucker growths extending over the leaves. The sucker growths can be removed manually, but this is a laborious and expensive proceeding. The use of sucker oil and chemicals, while effective in control of such secondary growth, nevertheless have in the past had serious disadvantages. The sucker oil tends to form leaf and stalk damage, causing soft spots that are attacked by microbes, and also there is a lack of control of the lower sucker stalks. The chemicals which have previously been used produce cellular changes in the leaf, tending to reduce the filling capacity of the treated tobacco for cigarette manufacture. Further, the cost of the chemicals has been high.

Cotton plants are customarily defoliated prior to mechanical picking. Such defoliation tends to encourage undesirable secondary growth which presents difliculties in mechanical picking and which must be separated from the cotton following mechanical picking. In periods of adverse weather preventing mechanical picking for several days, the secondary growth induced in the cotton plant treated with a defoliation agent tends to overcome the advantages of the original defoliation.

We have discovered that the undesirable secondary growth of plants can be effectively controlled through the spray application of primary, secondary or tertiary amine salts without entailing the disadvantages described above. The primary, secondary or tertiary amine salts can be applied in a coarse stream to the stem or other portion of the plant to effect a complete control of such sucker growth without plant injury.

ice

A primary object, therefore, of our invention is to provide a method for the treatment of plants for the control of undesirable secondary growth therein.

A further object is to provide for the control of undesirable secondary growth in tomato plants by applying to the plants control agents which prevent the secondary growth while at the same time avoiding injury to desirable portions of the plants.

A still further object is to provide for the control of undesirable secondary growth in soybean plants by applying to the plants control agents which prevent secondary growth while avoiding injury to desirable portions of the plants.

Another object is to provide for the control of undesirable secondary growth in cotton plants by applying to the plants control agents which prevent secondary growth while avoiding injury to desirable portions of the plants.

Other specific objects and advantages will appear as the specification proceeds.

In one embodiment of our invention, we apply to the plant primary, secondary or tertiary amine salts, including the organic and inorganic salts, in an aqueous solution or emulsion. For example, the amine salts may be applied in a coarse water spray directed to the stem of the plant, and such spray application is found to give effective control.

Such sucker control agents may be described by the following formula:

R is an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms;

R is selected from the group consisting of an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms, hydrogen, methyl, ethyl, ethoxy and propoxy;

R is selected from the group consisting of hydrogen, methyl, ethyl, ethoxy and propoxy, provided that when R is methyl, ethyl, ethoxy or propoxy R is the same as R X is an anion; and

n is an integer from 1 to 2 representing the number of acid functions neutralized.

The amine salts useful in our invention may be made by fully or partially neutralizing a mono or dibasic acid with a primary, secondary or tertiary amine.

The amomnium cation of the above formula is believed to be the effective sucker control agent and may be employed in combination with many anions. Examples are organic salts, such as acetates, levulinates, malonates, fumarates, tartarates, lactates, propionates, chloropropionates, succinates, phthalates, naphthenates, citrates, benzoates, etc., or inorganic salts, such as for example, nitrates, chlorides, sulfates, phosphates, etc. The free amines corresponding to the cationic portion of the above formula have shown effectiveness in control of secondary growth, but use of the salts is preferred due to greater effectiveness in control of secondary growth with lower phytotoxicity to the plants.

Specific examples illustrating the effectiveness and specific control methods may be set out as follows:

EXAMPLE I At the time of topping 3-15 ml. aqueous solutions were applied to the top of the plant and allowed to run down the stalk. T'he field results were as follows:

FLUE-CURED TOBACCO Conc.,

Material p.p.m. Sucker control Plant injury Dodecyldimethylamine acetate.

Dodeeylmethylamine acetate.

Satisfactory (85%) EXAMPLE II The method of application described in Example I was carried out on burley tobacco, and the field results were as follows:

EXAMPLE III A series of salts of cocodimethylamine were prepared and tested in the greenhouse for tobacco sucker control. At the time of flowering, the plants were topped and given an overall spray (20 ml. each). The concentrations of the treating salt varied between 0.125% and 0.5%. The effect at the different concentrations was observed at weekly intervals. The results were as follows:

Cocodimethylamine acetate at a concentration of 0.125% gave no sucker growth after a week but a slight sucker growth after two weeks. At a concentration of 0.5%, there was no sucker growth over a three-week interval.

Cocodimethylamine levulinate at concentrations of 0.125% and 0.25% gave no sucker growth after a week, but a slight growth after two weeks. At a concentration of 0.5%, there was no sucker growth observed over a three-week period.

Cocodirnethylamine malonate disalt at concentrations of 0.125% and at 0.25% gave no sucker growth after a week, but slight growth after two weeks. At a concentration of 0.5%, there was no sucker growth observed over a three-week period.

Cocodimethylamine phthalate disalt, at concentrations of 0.125 and 0.25 resulted in no sucker growth after a weeks interval, and a slight growth after a two-week interval. At a concentration of 0.5 there was no growth over a period of three weeks.

Cocodirnethylamine succinate-disalt produced no sucker growth for a week following treatment, but a slight growth after two weeks. At a concentration of 0.5%, there was no growth observed during a three-week interval.

Cocodimethylamine na-phthenate at concentrations of 0.125 and 0.25 gave slight sucker growth during one and two-week intervals, but at a concentration of 0.5%, there was no growth observed for the first two weeks after treatment and a slight growth observed after three weeks following treatment.

Cocodimethylamine nitrate at concentrations of 0.125 and .25% resulted in slight sucker growth during the first and second week intervals, but at a concentration of 0.5%, permitted no sucker growth over a three-week period.

Cocodimethylamine hydrochloride, at concentrations of 0.125 and .25 resulted in no sucker growth during the first week following treatment and slight growth at the end of the second week, 'but at a concentration of 0.5%, permitted no growth during a period of three weeks.

The untreated tobacco plant employed as a control in the above tests produced well-developed secondary shoots which were observed at each weekly inspection.

In the foregoing tests, no plant injury was observed.

EXAMPLE IV Flowering tobacco plants were topped and large suckers removed. The test plants were each sprayed with 20 m1. of an aqueous solution containing mg. of the active chemical. The spray was directed toward the stem. Twenty-one days following treatment the plants were observed and the following results obtained.

Sum of 2 plants, Percent suckers sucker control Green on basis Numweight, of green Plant Chemlcal ber grams weight injury Cocodirnethylamine a-chloro- 4 39. 2 84. 8 None.

propionate. Soya (polyoxyethylene-5 moles) 10 81. 2 68. 5 Do.

tertiary amine a-OhlOlO- propionate. Cocodimethylamine fi-chloro- 2 16. 7 93. 5 Do.

propionate. Coco-(polyoxyethylene-5 moles) 8 65. 5 74. 6 D0.

tgitiary amine succinate monos Oleyldlmethylamine succinate 6 125. 7 51. 3 Do.

monosalt. Soya (polyoxyethylene-5 moles) 10 94. 6 63. 3 Do.

tertiary amine isophthalate disalt. Cgcogllignethylamine fumarate 3 16. 1 93. 5 Do.

15 Control-No treatment 10 258. 0

The term polyoxyethylene-S moles refers to the adduct of 5 moles ethylene oxide per mole of amine.

EXAMPLE V Flowering Hicks tobacco plants were topped and the large suckers removed from the plant. The plants were each sprayed with 1.25 ml. of an aqueous solution containing 2500 p.p.rn. of active chemical. The plants were observed 13 days following application of the chemical.

and 1% wetting agent (Tween-20). Four plants were sprayed with each chemical and observed after fourteen days. The percent control is the percent by which treatment reduced sucker green weight compared to untreated controls.

Rate/plant Percent Chemical (mg) Tobacco type control Plant injury CH sec. alkyl primary 100 Burley 69.1 Very slight necrotic amine acetate. spots. 011- sec. alkyl primary 100 Connecticut Broadleaf 100 Moderate necrotic spots.

amine acetate. Cir-15 sec. alkyl dimethyl 100 Burley 99. 1 Do.

amine acetate. C sec. alkyl dirnethyl 100 do 100 Leaves normal.

amine oleate. 011-15 sec. alkyl dimethyl 100 Connecticut Broadlea-- 100 Do.

amine oleate. all-15 sec. alkyl dimethyl 50 Hicks Flue-Cured 97 Do.

amine oleate. Cir-15 sec. alkyl dimethyl 100 do 100 Do.

amine oleate. 011-15 sec. alkyl dimethyl 150 do 100 Leaves generally normal.

amine oleate. Cit-1 sec. alkyl primary 100 Connecticut Broadleaf. 100 Moderate necrotic spots.

amine eate. Cooodimethylamine 100 do 100 Slight necrotic spots.

chloropropionate.

C1 0 sec.-alkyl primary amine referee to amines obtained by the amidation of oletins as described in the pending application Ser. No. 397,287, filed Sept. 17, 1964.

EXAMPLE VII Cone, Presence Cotton plants were sprayed until thoroughly wet with Chemical p of Suclers milliliters or less of aqueous solutions of the below Control 10-12 lants Moderate to tablulated chemicals. The plants were observed for subp many,

Dodecyldimethylamine succinate monosalt.-- 500 None. sequent secondary growth sixteen days following spray D0 1 000 D0. application Of the chemicals. Cocodimethylamine citrate monosalt. 300 1lixew.

o 1, 00 one. Oleylamine succinate monosalt. 500 Few.

Do 1,000 None. Cone" presence Coccgiimethylamine maleate monosalt- 1 li lloderate. f ew. Chemical p p o suckers Cocodlm 500 Few. Control (2 plants) Moderate. 11000 Cocodimethylamine succinate monosalt 500 None. Cocodlm 500 Coco-(polyoxyethylene-Z moles) tertiary amine 1, 000 D0. 9 000 Nonesuccinate monosalt Cocodimethylamin su in e 500 Few, Small. 0 g 1 1 pn-mary amine succinate disalt 1, 000 D Cocopolyethoxylated-Z moles-amine succ at 500 Moderate, 011 015 sec.-alkyl primary amine citrate monosalt. 1,000 Do. mflnosfiltsmall 011-01, sec.-a1kyl primary amine citrate disalt 1,000 D0. D0 -T r 000 Few, Small- C r-C 5 sec.-alkyl primary amine tartrate disalt 1,000 Do. y pq v y moles-amine a- 500 None- 1 000 D propioiiate.

Coco (polyoxyethylene-5 moles) tertiary amine succinate disalt.

EXAMPLE VIII Soybean plants were sprayed until thoroughly wet with 20 milliliters or less of aqueous solutions of the below tabulated chemicals. The plants were observed for subsequent secondary growth fourteen days following spray application of the chemicals.

Conc., Presence Chemical p.p.m. oi suckers Control (10-12 plants) Moderate. Dodecyldimethylamine succinate monosalt. 500 Do.

Do 1,000 Few, None. Cocodimethylamine a chloropropionate. 500 Moderate. o 1,000 One. Dodecyldirnethylamine 9 chl0ropropi0nate 500 Few. Do 1, 000 Few. Soya-ethoxylated 5 moles-tertiary amine a 500 Few.

chloropropionate.

Do 1. 000 None. Tallowethoxylated 5 moles-tertiary amine 1, 000 D0.

succinate monosalt. Coco-ethoxylated 5 moles-tertiary amino 1, 000 Do.

succinate disalt. Oleyldirnethylamine succinate monosalt 1,000 Do. Hexadecyldimethylamine succinate monosalt 1,000 Do. Cocodimethylarnine tartarate monosalt 1,000 Do. Cocodimethylamine lactate 1,000 One. Oleylamine sucoinate disalt... 1,000 None. Tallowaniine succinate monosalt 1,000 Do. Cir-C115 secondary alkyl primary amine citrate l, 000 Do.

'sa t. Ci -C secondary alkyl primary amine succi- 1,000 Very few.

nate disalt.

EXAMPLE IX Tomato plants were sprayed until thoroughly wet with 20 milliliters or less of aqueous solutions of the below tabulated chemicals. The plants were observed for subsequent secondary growth sixteen days following spray application of the chemicals.

The concentration range of the particular active chemical used may vary widely depending upon various conditions, the type of plant being treated, age of the plant, etc. Generally, we find it suitable to use a concentration within the range of from about 0.01 to 10% which is effective for the control of undesirable secondary growth while at the same time avoiding plant injury, and best results have been obtained using concentrations of from about 0.05 to 1.0%.

Any suitable method of application of the active agent may be employed. We prefer to employ an aqueous solution and to direct the same onto the upper portion of the plant. For some purposes, an emulsion may be desired, and such an emulsion may be prepared by combining the chemical agents in a carrier using an emulsifier. By way of example, from 35% of Ethofat 60/15 (stearic acid containing 5 moles of ethylene oxide) may be combined with the agent and water to form an emulsion. Since the growth control compound is generally water soluble, the use of an equeous spray for most purposes will be preferred. Oil solutions or emulsions may be used in instances wherein the oil itself does not give rise to disadvantages. For example, oil has a deleterious effect upon desirable portions of tobacco plants.

While the foregoing specification has set out treating ingredients and procedural steps in considerable detail for the purpose of illustrating our invention, it will be understood that such detail or details may be varied by those skilled in the art without departing from the spirit of our invention.

We claim:

1. A method for treating growing cotton plants to control undesirable secondary growth therein without producing injury to desired portions of said plants, com- 7 prising applying to the plants an amine salt within the formula n|:Rz/NH+ :I-X

R is an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms,

R is selected from the group consisting of an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms, hydrogen, methyl, ethyl, ethoxy and pro- R is selected from the group consisting of hydrogen, methyl, ethyl, ethoxy, and propoxy, provided that when R; is methyl, ethyl, ethoxy or propoxy R is the same as R X is the anionic portion of an acid selected from the group consisting of inorganic and organic acids, and

n is an integer from 1 to 2 representing the number of acid functions neutralized;

said salt being applied in an amount effective to attain said control.

2. The method of claim 1 in which said aliphatic hydrocarbon radical is an alkyl radical.

3. The method of claim 1 in which the amine salt is applied in an aqueous solution.

4. The method of claim 1 in which the amine salt is applied in an oil solution.

5. The method of claim 1 in which the amine salt is applied as an emulsion.

6. The method Olf claim 1 in which the amine salt is dodecyldimethylamine acetate.

7. The method of claim 1 in which the amine salt is dodecylmethylamine acetate.

8. The method of claim 1 in which the amine salt is cocodimethylamine succinate mono-salt.

9. The method of claim 1 in which the amine salt is cocodimethylamine succinate disalt.

10. The method of claim 1 in which the amine salt is dodecyldimethylamine succinate monosalt.

11. The method of claim 1 in which the amine salt is cocodimethylamine chloropropionate.

12. The method of claim 1 in which the amine salt is cocodimethylamine fumarate.

13. A method for treating growing plants to control undesirable secondary growth without producing injury to desired portions of the plants, comprising applying to the plants an amine salt selected from the group consisting of oleylamine succinate, C -C secondary-alkyl primary amine oleate, and C C secondary-alkyl primary amine citrate.

14. A method for treating growing plants to control undesirable secondary growth therein without producing injury to desired portions of the plants, comprising applying to the plants an amine salt within the formula said salt being applied in an amount efiective'to attain said control.

15. The method of claim 14 wherein said plants are tobacco plants.

formula R1 n[ R2 NH+] -X"" R is an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms,

R is selected from the group consisting of an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms, hydrogen, methyl, ethyl, ethoxy and P P Y,

R is selected from the group consisting of hydrogen, methyl, ethyl, ethoxy and propoxy, provided that when R is methyl, ethyl, ethoxy or propoxy R is the same as R X is the anionic portion of an acid selected from the group consisting of inorganic and organic acids, and

n is an integer from 1 to 2 representing the number of acid lfunctions neutralized;

said salt being applied in an amount effective to attain said control.

17. The method of claim 16 in which said aliphatic hydrocarbon radical is an alkyl radical.

18. The method of claim 16 in which the amine is applied in an aqueous solution.

19. The method of claim 16 in which the amine is applied in an oil solution.

20. The method of claim 16 in which the amine is applied as an emulsion.

21. The method of claim 16 in which the amine is dodecyldimethylamine acetate.

22. The method of claim 16 in which the amine is dodecylmethylamine acetate.

23. The method of claim 16 in which the amine is cocodimethylamine succinate mono-salt.

24. The method of claim 16 in which the amint is cocodimethylamine succinate disalt.

25. The method of claim 16 in which the amine is dodecyldimethylamine succinate mono-salt.

26. The method of claim 16 in which the amine is cocodimethylamine chloropropionate.

27. The method of claim 16 in which the amine is cocodimethylamine fumarate.

28. A method for treating growing tomato plants to controlundesirable secondary growth therein without producing injury to desired portions of salt plants, comprising applying to the plants an amine salt within the formula R is an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms.

R is selected from the group consisting of an aliphatic hydrocarbon radical having from about 8 to 18 carbon atoms, hydrogen, methyl, ethyl, ethoxy and p p y R is selected from the group consisting of hydrogen, methyl, ethyl, ethoxy and propoxy, provided that when R is methyl, ethyl, ethoxy or propoxy R is the same as R X is the anionic portion of an acid selected from the group consisting of inorganic and organic acids, and

n is an integer from 1 to 2 representing the number of acid functions neutralized;

salt

salt

salt

salt

salt

salt

salt

salt

salt

salt

said salt being applied in an amount effective to attain said control. 7

29. The method of claim 28 in which said aliphatic hydrocarbon radical is an alkyl radical.

30. The method of claim 28 in which the is applied in an aqueous solution.

31. The method of claim 28 in which the is applied in an oil solution.

32. The method of claim 28 in which the is applied as an emulsion.

33. The method of claim 28 in which the is dodecyldimethylamine acetate.

34. The method of claim 28 in which the is dodecylmethylamine acetate.

35. The method of claim 28 in which the is cocodimethylamine succinate mono-salt.

36. The method of claim 28 in which the is cocodimethylamine succinate disalt.

37. The method of claim 28 in which the is dodecyldimethylamine succinate mono-salt.

38. The method of claim 28 in which the is cocodimethylamine chloropropionate.

39. The method of claim 28 in which the is cocodimethylamine fumarate.

40. The method of claim 14 wherein said plants tomato plants.

amine salt salt

salt

salt

salt

salt

salt

salt

salt

salt

are

4.1. The method of claim 14 wherein said plants are soybean plants.

42. The method of claim 14 wherein said plants are cotton plants.

5 References Cited UNITED STATES PATENTS 2,751,713 6/1956 Abramitis 71-27 X 2,970,048 1/1961 Hamm et a1 71 -2.5 3,156,555 11/1964 Tolbert 71-27 3,223,517 12/1965 Abramitis et al. 712.7

" OTHER REFERENCES Plant Regulators Publication 384, CBCC Positive Data 5 Series N0. 2, June 1955, pp. b, c, 1, 14 and 15.

' JAMES O. THOMAS, JR., Primary Examiner US. Cl. X.R. 20 71l21 

